ENANTIOSELECTIVE SYNTHESIS OF (3S,5R,6E,8E)-DECA-6,8-DIEN-1,3,5-TRIOL, A NEW METABOLITE FROM STREPTOMYCES-FIMBRIATUS VIA ASYMMETRIC REACTION OF DIKETENE WITH 2,4-HEXADIENAL PROMOTED BY CHIRAL SCHIFF BASE-TITANIUM ALKOXIDE COMPLEXES

被引：24

作者：

HAYASHI, M ^{[1
]}

KANEDA, H ^{[1
]}

OGUNI, N ^{[1
]}

机构：

[1] YAMAGUCHI UNIV,FAC SCI,DEPT CHEM,YAMAGUCHI 753,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 10期

关键词：

D O I：

10.1016/0957-4166(95)00328-M

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(3S,5R,6E,8E)-Deca-6,8-dien-1,3,5-triol, 6 which was isolated from the culture filtrate of Streptomyces fimbriatus has been synthesized efficiently via the enantioselective reaction of diketene with 2,4-hexadienal promoted by a novel chiral Schiff base-titanium alkoxide complex.

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页码：2511 / 2516

页数：6

相关论文

共 23 条

[1] A REMARKABLE SHORT SYNTHESIS OF OPTICALLY-ACTIVE MEVINIC ACID ANALOGS BY BIOCATALYTIC LACTONIZATION OF SYN-3,5-DIHYDROXY ESTERS [J].

BONINI, C ;

PUCCI, P ;

VIGGIANI, L .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :4050-4052

[2] A NEW STRATEGY FOR THE SYNTHESIS OF MEVINIC ACID ANALOGS [J].

BOQUEL, P ;

CHAPLEUR, Y .

TETRAHEDRON LETTERS, 1990, 31 (13) :1869-1872

[3] CRYSTAL AND MOLECULAR-STRUCTURE OF COMPACTIN, A NEW ANTIFUNGAL METABOLITE FROM PENICILLIUM-BREVICOMPACTUM [J].

BROWN, AG ;

SMALE, TC ;

KING, TJ ;

HASENKAMP, R ;

THOMPSON, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (11) :1165-1173

[4]

CASNATI G, Patent No. 5334737

[5] ML-236A, ML-236B, AND ML-236C, NEW INHIBITORS OF CHOLESTEROGENESIS PRODUCED BY PENICILLIUM CITRINUM [J].

ENDO, A ;

KURODA, M ;

TSUJITA, Y .

JOURNAL OF ANTIBIOTICS, 1976, 29 (12) :1346-1348

[6] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[7] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES CATALYZED BY CHIRAL SCHIFF-BASE TITANIUM ALKOXIDE COMPLEXES [J].

HAYASHI, M ;

MIYAMOTO, Y ;

INOUE, T ;

OGUNI, N .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1515-1522

[8] NOVEL ENANTIOSELECTIVE REACTION OF DIKETENE WITH ALDEHYDES PROMOTED BY CHIRAL SCHIFF BASE TITANIUM ALKOXIDE COMPLEX [J].

HAYASHI, M ;

INOUE, T ;

OGUNI, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :341-342

[9] ASYMMETRIC CARBON-CARBON BOND-FORMING REACTIONS CATALYZED BY CHIRAL SCHIFF BASE-TITANIUM ALKOXIDE COMPLEXES [J].

HAYASHI, M ;

INOUE, T ;

MIYAMOTO, Y ;

OGUNI, N .

TETRAHEDRON, 1994, 50 (15) :4385-4398

[10] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES BY CHIRAL TITANIUM SCHIFFS BASE COMPLEXES [J].

HAYASHI, M ;

MIYAMOTO, Y ;

INOUE, T ;

OGUNI, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (24) :1752-1753